# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3of_ligand
_database_code_depnum_ccdc_archive 'CCDC 1889567'
loop_
_audit_author_name
_audit_author_address
'Hasan Piskin'
;Gebze Technical University
Turkey
;
_audit_update_record             
;
2019-01-08 deposited with the CCDC.	2019-09-10 downloaded from the CCDC.
;
_audit_creation_date             2019-01-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H7 F3 N2 O2'
_chemical_formula_sum            'C15 H7 F3 N2 O2'
_chemical_formula_weight         304.23
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.9064(13)
_cell_length_b                   8.1423(11)
_cell_length_c                   11.5605(17)
_cell_angle_alpha                98.881(10)
_cell_angle_beta                 106.291(11)
_cell_angle_gamma                95.593(13)
_cell_volume                     697.96(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1021
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.27
_cell_measurement_theta_min      2.56
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.970
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6503
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             308
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.245
_exptl_crystal_size_mid          0.045
_exptl_crystal_size_min          0.043
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_unetI/netI     0.0546
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6811
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.017
_diffrn_reflns_theta_max         25.017
_diffrn_reflns_theta_min         1.869
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  
'Bruker APEX II QUAZAR three-circle diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multilayer QUAZAR mirrors'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source_type              ImuS
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1299
_reflns_number_total             2467
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'APEX2 v2014.9-0 (Bruker AXS)'
_computing_data_collection       
'Bruker Instrument Service v2013.12.0.0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2015)'
_refine_diff_density_max         0.522
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.033(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2467
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1298
_refine_ls_R_factor_gt           0.0710
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0833P)²+0.6032P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1823
_refine_ls_wR_factor_ref         0.2198
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1270(4) 0.0603(4) 0.6961(3) 0.0752(10) Uani 1 1 d . . . . .
O2 O 0.6582(5) 0.4707(4) 0.6126(3) 0.0811(10) Uani 1 1 d . . . . .
C6 C 0.0392(5) -0.1021(5) 0.8238(4) 0.0506(10) Uani 1 1 d . . . . .
C1 C 0.1737(5) -0.0417(5) 0.7792(4) 0.0549(11) Uani 1 1 d . . . . .
C5 C 0.0745(5) -0.2102(5) 0.9074(4) 0.0556(11) Uani 1 1 d . . . . .
C9 C 0.2655(5) 0.1616(5) 0.6751(4) 0.0605(11) Uani 1 1 d . . . . .
C12 C 0.5269(6) 0.3590(5) 0.6334(4) 0.0614(12) Uani 1 1 d . . . . .
C2 C 0.3405(6) -0.0893(6) 0.8179(5) 0.0655(13) Uani 1 1 d . . . . .
C11 C 0.4339(7) 0.2251(6) 0.5454(5) 0.0686(13) Uani 1 1 d . . . . .
F2 F 0.9212(5) 0.5508(4) 0.6092(4) 0.1235(13) Uani 1 1 d . . . . .
C10 C 0.3005(6) 0.1233(6) 0.5663(5) 0.0652(12) Uani 1 1 d . . . . .
C7 C -0.0652(6) -0.2736(5) 0.9531(4) 0.0631(12) Uani 1 1 d . . . . .
C4 C 0.2419(7) -0.2566(6) 0.9453(5) 0.0737(14) Uani 1 1 d . . . . .
C8 C -0.1327(6) -0.0508(6) 0.7865(4) 0.0603(11) Uani 1 1 d . . . . .
C3 C 0.3731(7) -0.1951(6) 0.9009(5) 0.0752(15) Uani 1 1 d . . . . .
N1 N -0.1772(6) -0.3215(5) 0.9886(4) 0.0820(13) Uani 1 1 d . . . . .
C14 C 0.3565(7) 0.2973(7) 0.7616(5) 0.0806(16) Uani 1 1 d . . . . .
N2 N -0.2714(6) -0.0124(6) 0.7589(4) 0.0860(13) Uani 1 1 d . . . . .
F3 F 0.8859(5) 0.3825(7) 0.7225(6) 0.178(2) Uani 1 1 d . . . . .
C13 C 0.4892(7) 0.3987(7) 0.7403(5) 0.0756(14) Uani 1 1 d . . . . .
F1 F 0.8134(7) 0.3002(6) 0.5389(7) 0.222(3) Uani 1 1 d . . . . .
C15 C 0.8090(9) 0.4273(7) 0.6136(7) 0.0954(18) Uani 1 1 d . . . . .
H2 H 0.427(6) -0.049(5) 0.784(4) 0.067(12) Uiso 1 1 d . . . . .
H10 H 0.232(6) 0.030(6) 0.505(4) 0.079(14) Uiso 1 1 d . . . . .
H3 H 0.486(7) -0.222(6) 0.922(4) 0.080(15) Uiso 1 1 d . . . . .
H11 H 0.462(6) 0.192(6) 0.481(4) 0.080(16) Uiso 1 1 d . . . . .
H14 H 0.337(7) 0.315(6) 0.830(5) 0.094(18) Uiso 1 1 d . . . . .
H13 H 0.566(7) 0.493(6) 0.797(5) 0.094(16) Uiso 1 1 d . . . . .
H4 H 0.257(6) -0.321(5) 0.998(4) 0.072(15) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.363(5) . ?
O1 C9 1.404(5) . ?
O2 C12 1.409(5) . ?
O2 C15 1.274(7) . ?
C6 C1 1.386(5) . ?
C6 C5 1.395(5) . ?
C6 C8 1.431(6) . ?
C1 C2 1.383(6) . ?
C5 C7 1.437(6) . ?
C5 C4 1.381(6) . ?
C9 C10 1.359(6) . ?
C9 C14 1.356(7) . ?
C12 C11 1.359(6) . ?
C12 C13 1.351(6) . ?
C2 C3 1.375(7) . ?
C2 H2 0.93(4) . ?
C11 C10 1.376(6) . ?
C11 H11 0.85(5) . ?
F2 C15 1.292(5) . ?
C10 H10 0.95(5) . ?
C7 N1 1.137(5) . ?
C4 C3 1.367(7) . ?
C4 H4 0.86(4) . ?
C8 N2 1.142(5) . ?
C3 H3 0.91(5) . ?
C14 C13 1.372(7) . ?
C14 H14 0.85(5) . ?
F3 C15 1.357(7) . ?
C13 H13 0.96(5) . ?
F1 C15 1.251(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C9 117.3(3) . . ?
C15 O2 C12 120.3(4) . . ?
C1 C6 C5 119.3(4) . . ?
C1 C6 C8 120.2(4) . . ?
C5 C6 C8 120.4(3) . . ?
O1 C1 C6 115.6(4) . . ?
O1 C1 C2 124.7(4) . . ?
C2 C1 C6 119.7(4) . . ?
C6 C5 C7 119.3(4) . . ?
C4 C5 C6 120.3(4) . . ?
C4 C5 C7 120.4(4) . . ?
C10 C9 O1 118.7(4) . . ?
C14 C9 O1 119.5(4) . . ?
C14 C9 C10 121.8(4) . . ?
C11 C12 O2 121.0(4) . . ?
C13 C12 O2 116.9(4) . . ?
C13 C12 C11 121.9(4) . . ?
C1 C2 H2 117(3) . . ?
C3 C2 C1 120.1(4) . . ?
C3 C2 H2 122(3) . . ?
C12 C11 C10 119.5(5) . . ?
C12 C11 H11 123(3) . . ?
C10 C11 H11 117(3) . . ?
C9 C10 C11 118.3(5) . . ?
C9 C10 H10 121(3) . . ?
C11 C10 H10 121(3) . . ?
N1 C7 C5 178.8(5) . . ?
C5 C4 H4 116(3) . . ?
C3 C4 C5 119.6(5) . . ?
C3 C4 H4 124(3) . . ?
N2 C8 C6 178.1(5) . . ?
C2 C3 H3 115(3) . . ?
C4 C3 C2 120.9(5) . . ?
C4 C3 H3 124(3) . . ?
C9 C14 C13 119.6(5) . . ?
C9 C14 H14 120(4) . . ?
C13 C14 H14 120(4) . . ?
C12 C13 C14 118.7(5) . . ?
C12 C13 H13 115(3) . . ?
C14 C13 H13 126(3) . . ?
O2 C15 F2 112.3(5) . . ?
O2 C15 F3 109.5(5) . . ?
F2 C15 F3 104.0(6) . . ?
F1 C15 O2 118.6(6) . . ?
F1 C15 F2 109.5(5) . . ?
F1 C15 F3 101.5(7) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C2 H2 N2 0.93(4) 2.48(4) 3.347(6) 155(3) 1_655 yes
C10 H10 F1 0.95(5) 2.63(4) 3.416(6) 140(3) 2_656 yes
C13 H13 N1 0.96(5) 2.67(5) 3.598(7) 162(4) 1_665 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -178.9(4) . . . . ?
O1 C9 C10 C11 178.7(4) . . . . ?
O1 C9 C14 C13 -178.5(5) . . . . ?
O2 C12 C11 C10 -176.7(4) . . . . ?
O2 C12 C13 C14 177.1(5) . . . . ?
C6 C1 C2 C3 -0.4(7) . . . . ?
C6 C5 C4 C3 0.4(7) . . . . ?
C1 O1 C9 C10 108.8(5) . . . . ?
C1 O1 C9 C14 -73.3(6) . . . . ?
C1 C6 C5 C7 -179.6(4) . . . . ?
C1 C6 C5 C4 0.0(6) . . . . ?
C1 C2 C3 C4 0.8(8) . . . . ?
C5 C6 C1 O1 178.7(3) . . . . ?
C5 C6 C1 C2 0.0(6) . . . . ?
C5 C4 C3 C2 -0.8(8) . . . . ?
C9 O1 C1 C6 162.2(4) . . . . ?
C9 O1 C1 C2 -19.2(6) . . . . ?
C9 C14 C13 C12 -0.8(8) . . . . ?
C12 O2 C15 F2 -171.5(4) . . . . ?
C12 O2 C15 F3 -56.5(7) . . . . ?
C12 O2 C15 F1 59.2(9) . . . . ?
C12 C11 C10 C9 0.4(7) . . . . ?
C11 C12 C13 C14 2.1(8) . . . . ?
C10 C9 C14 C13 -0.7(8) . . . . ?
C7 C5 C4 C3 180.0(4) . . . . ?
C8 C6 C1 O1 -2.7(6) . . . . ?
C8 C6 C1 C2 178.6(4) . . . . ?
C8 C6 C5 C7 1.8(6) . . . . ?
C8 C6 C5 C4 -178.6(4) . . . . ?
C14 C9 C10 C11 0.9(8) . . . . ?
C13 C12 C11 C10 -1.9(8) . . . . ?
C15 O2 C12 C11 -74.8(7) . . . . ?
C15 O2 C12 C13 110.2(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
